The Highlands Land for Sale

Welcome to The Highlands, a stunning subdivision nestled in the picturesque town of Winchester, Tennessee, within the heart of Franklin County. This enchanting community offers a unique blend of natural beauty and modern living, making it an ideal place for those seeking to build their dream home or invest in prime land.

The Highlands is characterized by its rolling hills, serene landscapes, and abundant greenery, providing a tranquil escape from the hustle and bustle of city life. Residents here enjoy a peaceful atmosphere, complemented by a friendly neighborhood vibe that fosters a sense of belonging. With its close-knit community, The Highlands is perfect for families, retirees, and anyone looking to enjoy the simple pleasures of life.

Currently, we have an array of beautiful land for sale in The Highlands, offering you the perfect canvas to create your ideal living space. Whether you're envisioning a cozy cottage or a sprawling estate, the generous lots available provide ample room for your dreams to flourish. Each parcel is thoughtfully situated to maximize privacy while still being within reach of local amenities, schools, and recreational opportunities.

In addition to its scenic beauty, The Highlands is conveniently located near Winchester's charming downtown area, where you can find delightful shops, restaurants, and community events. With easy access to nearby parks and outdoor activities, this subdivision is a haven for nature lovers and adventure seekers alike.

Don't miss your chance to be part of this exceptional community. Explore the land for sale in The Highlands today and start envisioning your future in this beautiful Tennessee setting!

Newest The Highlands Land for Sale

$2,250,000

3500774 MLS ⋅ ACTIVE Status ⋅ 15.65 Acres ⋅ 37179 Zip Code

Set within the rolling landscape of Middle Tennessee, this approximately 15.65-acre homesite in The Highlands offers a rare opportunity to create an estate that is deeply connected to the land. Framed by sweeping Tennessee vistas and natural beauty in every direction, the property provides an extraordinary canvas for a custom residence where timeless architecture and the surrounding landscape exist in perfect harmony. The property features two primary homesites, each accommodating up to six bedrooms, along with an accessory homesite for a two-bedroom guest house, pool house, studio, or additional living space, providing exceptional flexibility to create a private family compound or a one-of-a-kind retreat tailored to your lifestyle. Property features include an old tobacco barn and hay barn, which could easily be transformed into an indoor wellness center, as well as creeks and a pond. With expansive acreage, remarkable privacy, and sweeping Tennessee vistas, the property offers endless opportunities for outdoor living, recreation, gardens, equestrian use, and resort-style amenities. It is an ideal canvas for creating a legacy property designed to be enjoyed for generations. Conveniently located just minutes from historic downtown Franklin, Leiper's Fork, Williamson County schools, shopping, and dining, this property offers the perfect balance of peaceful country living and everyday convenience. Bring your own builder and vision, or collaborate with the established builder and design team. For inspiration, explore the stunning residence planned for 1914 Thompson's Station Road West, Lot 2, or create a fully custom estate that reflects your own vision and lifestyle.

1914 W Thompsons Station Rd, Thompsons Station

$3,000,000

3287541 MLS ⋅ ACTIVE Status ⋅ 20 Acres ⋅ 37179 Zip Code

Experience pristine Tennessee living on 20 breathtaking acres in The Highlands, where rolling hills, panoramic views, and the natural beauty of Middle Tennessee create an extraordinary setting for a legacy estate. Thoughtfully positioned to complement the surrounding landscape, this exceptional parcel offers a rare opportunity to create a timeless custom residence that feels as though it has always belonged. Beyond the featured residence, the property is approved for two primary residences, each accommodating six or more bedrooms, providing exceptional flexibility to create a multigenerational family compound, private guest residences, or a lasting legacy estate. With expansive acreage, remarkable privacy, and sweeping Tennessee vistas, the property offers endless possibilities for outdoor living, recreation, gardens, equestrian use, and multigenerational living. It is an ideal canvas for creating a one-of-a-kind retreat designed to be enjoyed for generations. Conveniently located just minutes from historic downtown Franklin, Leiper’s Fork, Williamson County schools, shopping, and dining, this property offers the perfect balance of peaceful country living and everyday accessibility. Bring your own builder and vision, or work with the established builder and design team. For inspiration, explore the stunning residence planned for 1914 Thompson’s Station Road West, Lot 1, or create an entirely custom home tailored to your lifestyle.

1914 W Thompsons Station Rd, Thompsons Station

$57,900

2792698 MLS ⋅ ACTIVE Status ⋅ 0.55 Acres ⋅ 37398 Zip Code

New Gated Community, The Highlands! Located less than one minute from Tims Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining.

66 Edgefield Ct, Winchester

$57,900

2792697 MLS ⋅ ACTIVE Status ⋅ 0.28 Acres ⋅ 37398 Zip Code

New Gated Community, The Highlands! Located less than one minute from Tims Ford Lake (public boat launch on Sharp Springs Rd). Convenient to shopping and dining. Underground utilities and security gate.

67 Edgefield Ct, Winchester

Start Your Search

Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.